# electronic Ligand Builder and Optimisation Workbench (eLBOW)
#   - a module of PHENIX version dev-svn-
#   - file written: Wed Apr  1 22:15:49 2020
#   Inital geometry file: a 141 line input string
#   Ligand name: (4S)-6-amino-4-(5-cyano-3'-fluorobiphenyl-3-yl)-4-cyclobutyl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile
#   Quantum optimisation: True
#   Method: PBEh-3c
#   Random seed: 3628800
#   SMILES string: Cc1[nH]nc2OC(=C(C#N)[C@](C3CCC3)(c4cc(cc(c4)c5cccc(F)c5)C#N)c12)N
#
data_comp_list
loop_
_chem_comp.id
_chem_comp.three_letter_code
_chem_comp.name
_chem_comp.group
_chem_comp.number_atoms_all
_chem_comp.number_atoms_nh
_chem_comp.desc_level
_chem_comp.initial_date
_chem_comp.modified_date
_chem_comp.source
 33G  33G  (4S)-6-amino-4-(5-cyano-3'-fluorobiphenyl-3-yl)-4-cyclobutyl-3-methyl-2,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile  ligand  52  32  .  2022-07-22  2022-07-26
;
Directly from eLBOW using geometry from QM method PBEh-3c with CPCM solvent model
Validated by Mogul as OK (reasonable std)
;

data_comp_33G
loop_
_chem_comp_atom.comp_id
_chem_comp_atom.atom_id
_chem_comp_atom.type_symbol
_chem_comp_atom.type_energy
_chem_comp_atom.charge
_chem_comp_atom.partial_charge
_chem_comp_atom.x
_chem_comp_atom.y
_chem_comp_atom.z
 33G  F32  F  F     0  -0.314  -6.4551   0.4433   1.5498
 33G  C30  C  CR6   0   0.552  -5.4049   0.7565   0.7751
 33G  C29  C  CR16  0  -0.417  -5.4717   1.8894  -0.0125
 33G  C28  C  CR16  0  -0.225  -4.3726   2.2000  -0.8009
 33G  C27  C  CR16  0  -0.316  -3.2447   1.3937  -0.7938
 33G  C31  C  CR16  0  -0.475  -4.2960  -0.0648   0.8041
 33G  C26  C  CR6   0   0.106  -3.1954   0.2537   0.0090
 33G  C22  C  CR6   0   0.126  -1.9978  -0.6097   0.0125
 33G  C21  C  CR16  0  -0.329  -2.1177  -1.9943   0.1014
 33G  C20  C  CR6   0   0.065  -0.9730  -2.7794   0.0844
 33G  C24  C  CSP   0   0.049  -1.0962  -4.1997   0.1672
 33G  N25  N  NS    0  -0.247  -1.1922  -5.3459   0.2340
 33G  C19  C  CR16  0  -0.353   0.2981  -2.2113  -0.0254
 33G  C23  C  CR16  0  -0.324  -0.7258  -0.0563  -0.0858
 33G  C18  C  CR6   0   0.211   0.4287  -0.8354  -0.1125
 33G  C4   C  CR6   0  -0.182   1.7844  -0.1348  -0.1968
 33G  C3   C  CR6   0  -0.229   1.7402   0.9062  -1.3134
 33G  C8   C  CSP   0   0.027   1.1791   0.5441  -2.5503
 33G  N9   N  NS    0  -0.285   0.6975   0.2583  -3.5644
 33G  C2   C  CR6   0   0.613   2.2020   2.1955  -1.2022
 33G  N7   N  NH2   0  -0.832   2.3158   3.0734  -2.2052
 33G  C14  C  C     0  -0.213   2.9518  -1.1207  -0.3708
 33G  C17  C  C     0  -0.448   3.1624  -1.9429  -1.6602
 33G  C16  C  C     0  -0.449   4.6781  -1.7523  -1.4676
 33G  C15  C  C     0  -0.431   4.3728  -0.5572  -0.5438
 33G  C5   C  CR56  0  -0.146   2.0211   0.6420   1.0617
 33G  C10  C  CR5   0   0.365   1.9673   0.3242   2.4077
 33G  C13  C  CH3   0  -0.749   1.5976  -0.9286   3.1146
 33G  N11  N  NR15  0  -0.491   2.3411   1.4418   3.0552
 33G  N12  N  N     0  -0.293   2.6351   2.4693   2.2527
 33G  C6   C  CR56  0   0.460   2.4388   1.9675   1.0624
 33G  O1   O  O     0  -0.453   2.6329   2.7223  -0.0456
 33G  H1   H  HCR6  0   0.284  -6.3573   2.5107  -0.0126
 33G  H2   H  HCR6  0   0.274  -4.4017   3.0775  -1.4327
 33G  H3   H  HCR6  0   0.259  -2.4104   1.6437  -1.4366
 33G  H4   H  HCR6  0   0.281  -4.2843  -0.9300   1.4550
 33G  H5   H  HCR6  0   0.283  -3.0910  -2.4633   0.1617
 33G  H6   H  HCR6  0   0.281   1.1585  -2.8643  -0.0342
 33G  H7   H  HCR6  0   0.266  -0.6226   1.0215  -0.1284
 33G  H10  H  HNH2  0   0.421   1.9844   2.8316  -3.1239
 33G  H11  H  HNH2  0   0.418   2.3507   4.0584  -1.9959
 33G  H13  H  H     0   0.247   2.9598  -1.7988   0.4890
 33G  H14  H  H     0   0.234   2.7762  -2.9624  -1.6788
 33G  H15  H  H     0   0.238   2.8063  -1.4243  -2.5496
 33G  H16  H  H     0   0.229   5.1213  -2.5841  -0.9190
 33G  H17  H  H     0   0.232   5.2784  -1.5603  -2.3563
 33G  H18  H  H     0   0.228   4.3734   0.3788  -1.1054
 33G  H19  H  H     0   0.236   4.9789  -0.4328   0.3530
 33G  H20  H  HCH3  0   0.264   2.3362  -1.7122   2.9437
 33G  H21  H  HCH3  0   0.269   1.5280  -0.7694   4.1897
 33G  H22  H  HCH3  0   0.262   0.6345  -1.3019   2.7674
 33G  H23  H  HNR5  0   0.423   2.4052   1.5642   4.0535

loop_
_chem_comp_bond.comp_id
_chem_comp_bond.atom_id_1
_chem_comp_bond.atom_id_2
_chem_comp_bond.type
_chem_comp_bond.value_dist
_chem_comp_bond.value_dist_esd
_chem_comp_bond.value_dist_neutron
 33G  N25  C24  triple    1.152  0.020  1.152
 33G  N9   C8   triple    1.158  0.020  1.158
 33G  C16  C15  single    1.541  0.020  1.541
 33G  C16  C17  single    1.540  0.020  1.540
 33G  C24  C20  single    1.428  0.020  1.428
 33G  C8   C3   single    1.406  0.020  1.406
 33G  C15  C14  single    1.538  0.020  1.538
 33G  C20  C19  aromatic  1.397  0.020  1.397
 33G  C20  C21  aromatic  1.388  0.020  1.388
 33G  C19  C18  aromatic  1.385  0.020  1.385
 33G  N7   C2   single    1.338  0.020  1.338
 33G  C17  C14  single    1.544  0.020  1.544
 33G  C3   C2   double    1.374  0.020  1.374
 33G  C3   C4   single    1.527  0.020  1.527
 33G  C14  C4   single    1.538  0.020  1.538
 33G  C2   O1   single    1.342  0.020  1.342
 33G  C21  C22  aromatic  1.393  0.020  1.393
 33G  C18  C4   single    1.528  0.020  1.528
 33G  C18  C23  aromatic  1.393  0.020  1.393
 33G  C4   C5   single    1.498  0.020  1.498
 33G  C23  C22  aromatic  1.391  0.020  1.391
 33G  C22  C26  single    1.476  0.020  1.476
 33G  O1   C6   single    1.355  0.020  1.355
 33G  C5   C6   aromatic  1.390  0.020  1.390
 33G  C5   C10  aromatic  1.384  0.020  1.384
 33G  C6   N12  aromatic  1.307  0.020  1.307
 33G  C31  C26  aromatic  1.395  0.020  1.395
 33G  C31  C30  aromatic  1.380  0.020  1.380
 33G  C26  C27  aromatic  1.395  0.020  1.395
 33G  C10  C13  single    1.485  0.020  1.485
 33G  C10  N11  aromatic  1.345  0.020  1.345
 33G  F32  C30  single    1.342  0.020  1.342
 33G  N12  N11  aromatic  1.336  0.020  1.336
 33G  C30  C29  aromatic  1.381  0.020  1.381
 33G  C27  C28  aromatic  1.387  0.020  1.387
 33G  C29  C28  aromatic  1.388  0.020  1.388
 33G  C29  H1   single    0.930  0.020  1.080
 33G  C28  H2   single    0.930  0.020  1.080
 33G  C27  H3   single    0.930  0.020  1.080
 33G  C31  H4   single    0.930  0.020  1.080
 33G  C21  H5   single    0.930  0.020  1.080
 33G  C19  H6   single    0.930  0.020  1.080
 33G  C23  H7   single    0.930  0.020  1.080
 33G  N7   H10  single    0.890  0.020  1.040
 33G  N7   H11  single    0.890  0.020  1.040
 33G  C14  H13  single    0.970  0.020  1.090
 33G  C17  H14  single    0.970  0.020  1.090
 33G  C17  H15  single    0.970  0.020  1.090
 33G  C16  H16  single    0.970  0.020  1.090
 33G  C16  H17  single    0.970  0.020  1.090
 33G  C15  H18  single    0.970  0.020  1.090
 33G  C15  H19  single    0.970  0.020  1.090
 33G  C13  H20  single    0.970  0.020  1.090
 33G  C13  H21  single    0.970  0.020  1.090
 33G  C13  H22  single    0.970  0.020  1.090
 33G  N11  H23  single    0.860  0.020  1.020

loop_
_chem_comp_angle.comp_id
_chem_comp_angle.atom_id_1
_chem_comp_angle.atom_id_2
_chem_comp_angle.atom_id_3
_chem_comp_angle.value_angle
_chem_comp_angle.value_angle_esd
 33G  C31  C30  C29  122.61  3.000
 33G  C29  C30  F32  118.86  3.000
 33G  C31  C30  F32  118.53  3.000
 33G  H1   C29  C28  121.31  3.000
 33G  H1   C29  C30  120.71  3.000
 33G  C28  C29  C30  117.98  3.000
 33G  H2   C28  C27  119.78  3.000
 33G  H2   C28  C29  119.48  3.000
 33G  C27  C28  C29  120.74  3.000
 33G  H3   C27  C26  120.21  3.000
 33G  H3   C27  C28  119.31  3.000
 33G  C26  C27  C28  120.46  3.000
 33G  H4   C31  C26  121.11  3.000
 33G  H4   C31  C30  119.79  3.000
 33G  C26  C31  C30  119.09  3.000
 33G  C22  C26  C31  120.35  3.000
 33G  C31  C26  C27  119.13  3.000
 33G  C22  C26  C27  120.52  3.000
 33G  C23  C22  C21  118.62  3.000
 33G  C23  C22  C26  120.60  3.000
 33G  C21  C22  C26  120.78  3.000
 33G  H5   C21  C20  119.82  3.000
 33G  H5   C21  C22  120.79  3.000
 33G  C20  C21  C22  119.37  3.000
 33G  C19  C20  C24  119.19  3.000
 33G  C19  C20  C21  121.43  3.000
 33G  C24  C20  C21  119.38  3.000
 33G  N25  C24  C20  180.00  3.000
 33G  H6   C19  C18  121.68  3.000
 33G  H6   C19  C20  118.66  3.000
 33G  C18  C19  C20  119.67  3.000
 33G  H7   C23  C18  118.46  3.000
 33G  H7   C23  C22  119.06  3.000
 33G  C18  C23  C22  122.47  3.000
 33G  C4   C18  C23  118.68  3.000
 33G  C23  C18  C19  118.45  3.000
 33G  C4   C18  C19  122.85  3.000
 33G  C5   C4   C14  107.91  3.000
 33G  C5   C4   C3   105.39  3.000
 33G  C14  C4   C3   112.10  3.000
 33G  C5   C4   C18  109.36  3.000
 33G  C14  C4   C18  112.69  3.000
 33G  C3   C4   C18  109.09  3.000
 33G  C2   C3   C8   116.56  3.000
 33G  C2   C3   C4   124.80  3.000
 33G  C8   C3   C4   118.64  3.000
 33G  N9   C8   C3   180.00  3.000
 33G  O1   C2   N7   111.18  3.000
 33G  O1   C2   C3   123.10  3.000
 33G  N7   C2   C3   125.71  3.000
 33G  H11  N7   H10  115.85  3.000
 33G  H11  N7   C2   119.25  3.000
 33G  H10  N7   C2   119.92  3.000
 33G  H13  C14  C15  107.96  3.000
 33G  H13  C14  C17  108.97  3.000
 33G  C15  C14  C17   88.58  3.000
 33G  H13  C14  C4   108.28  3.000
 33G  C17  C14  C4   122.65  3.000
 33G  C15  C14  C4   118.62  3.000
 33G  H15  C17  H14  108.38  3.000
 33G  H15  C17  C16  111.40  3.000
 33G  H14  C17  C16  117.82  3.000
 33G  H15  C17  C14  112.57  3.000
 33G  H14  C17  C14  117.64  3.000
 33G  C16  C17  C14   87.93  3.000
 33G  H17  C16  H16  108.71  3.000
 33G  H17  C16  C15  117.49  3.000
 33G  H16  C16  C15  111.74  3.000
 33G  H17  C16  C17  117.53  3.000
 33G  H16  C16  C17  111.62  3.000
 33G  C15  C16  C17   88.62  3.000
 33G  H19  C15  H18  108.98  3.000
 33G  H19  C15  C16  118.15  3.000
 33G  H18  C15  C16  110.88  3.000
 33G  H19  C15  C14  117.59  3.000
 33G  H18  C15  C14  111.87  3.000
 33G  C16  C15  C14   88.07  3.000
 33G  C6   C5   C10  103.31  3.000
 33G  C10  C5   C4   133.78  3.000
 33G  C6   C5   C4   122.86  3.000
 33G  N11  C10  C13  122.76  3.000
 33G  N11  C10  C5   105.46  3.000
 33G  C13  C10  C5   131.78  3.000
 33G  H22  C13  H21  107.95  3.000
 33G  H22  C13  H20  107.61  3.000
 33G  H21  C13  H20  107.65  3.000
 33G  H22  C13  C10  110.93  3.000
 33G  H21  C13  C10  111.25  3.000
 33G  H20  C13  C10  111.28  3.000
 33G  H23  N11  N12  119.17  3.000
 33G  H23  N11  C10  126.56  3.000
 33G  N12  N11  C10  114.27  3.000
 33G  C6   N12  N11  102.63  3.000
 33G  O1   C6   N12  120.64  3.000
 33G  N12  C6   C5   114.32  3.000
 33G  O1   C6   C5   125.04  3.000
 33G  C6   O1   C2   116.12  3.000

loop_
_chem_comp_tor.comp_id
_chem_comp_tor.id
_chem_comp_tor.atom_id_1
_chem_comp_tor.atom_id_2
_chem_comp_tor.atom_id_3
_chem_comp_tor.atom_id_4
_chem_comp_tor.value_angle
_chem_comp_tor.value_angle_esd
_chem_comp_tor.period
 33G  CONST_01  C22  C26  C31  C30  180.00   0.0  0
 33G  CONST_02  C27  C26  C31  C30    0.00   0.0  0
 33G  CONST_03  C27  C28  C29  C30    0.00   0.0  0
 33G  CONST_04  C26  C31  C30  C29    0.00   0.0  0
 33G  CONST_05  C26  C27  C28  C29    0.00   0.0  0
 33G  CONST_06  C22  C26  C27  C28  180.00   0.0  0
 33G  CONST_07  C31  C26  C27  C28    0.00   0.0  0
 33G  CONST_08  C31  C30  C29  C28    0.00   0.0  0
 33G  CONST_13  C20  C21  C22  C26  180.00   0.0  0
 33G  CONST_14  C18  C23  C22  C26  180.00   0.0  0
 33G  CONST_15  C19  C20  C21  C22    0.00   0.0  0
 33G  CONST_16  C19  C18  C23  C22    0.00   0.0  0
 33G  CONST_17  C18  C19  C20  C21    0.00   0.0  0
 33G  CONST_18  C18  C23  C22  C21    0.00   0.0  0
 33G  CONST_19  C23  C18  C19  C20    0.00   0.0  0
 33G  CONST_20  C23  C22  C21  C20    0.00   0.0  0
 33G  CONST_21  N11  N12  C6   C5     0.00   0.0  0
 33G  CONST_22  N12  N11  C10  C5     0.00   0.0  0
 33G  CONST_23  N12  C6   C5   C10    0.00   0.0  0
 33G  CONST_24  C6   N12  N11  C10    0.00   0.0  0
 33G  CONST_25  C6   C5   C10  N11    0.00   0.0  0
 33G  CONST_26  C4   C18  C23  C22  180.00   0.0  0
 33G  CONST_27  C4   C18  C19  C20  180.00   0.0  0
 33G  CONST_28  C26  C31  C30  F32  180.00   0.0  0
 33G  CONST_29  C28  C29  C30  F32  180.00   0.0  0
 33G  CONST_30  C24  C20  C21  C22  180.00   0.0  0
 33G  CONST_31  C18  C19  C20  C24  180.00   0.0  0
 33G  CONST_32  C13  C10  C5   C4     0.00   0.0  0
 33G  CONST_33  C6   C5   C10  C13  180.00   0.0  0
 33G  CONST_34  N12  N11  C10  C13  180.00   0.0  0
 33G  CONST_35  H2   C28  C29  C30  180.00   0.0  0
 33G  CONST_36  H4   C31  C30  C29  180.00   0.0  0
 33G  CONST_37  H3   C27  C28  C29  180.00   0.0  0
 33G  CONST_38  H1   C29  C28  C27  180.00   0.0  0
 33G  CONST_39  H5   C21  C22  C26    0.00   0.0  0
 33G  CONST_40  H7   C23  C22  C26    0.00   0.0  0
 33G  CONST_41  H6   C19  C20  C21  180.00   0.0  0
 33G  CONST_42  H23  N11  C10  C5   180.00   0.0  0
 33G  Var_01    O1   C2   C3   C4    -6.55  30.0  1
 33G  Var_02    C5   C6   O1   C2     9.99  30.0  1
 33G  Var_03    C17  C16  C15  C14   19.58  30.0  1
 33G  Var_04    C2   C3   C8   N9   -74.31  30.0  3
 33G  Var_05    H10  N7   C2   C3     4.77  30.0  2
 33G  Var_06    H20  C13  C10  C5    68.41  30.0  2

loop_
_chem_comp_chir.comp_id
_chem_comp_chir.id
_chem_comp_chir.atom_id_centre
_chem_comp_chir.atom_id_1
_chem_comp_chir.atom_id_2
_chem_comp_chir.atom_id_3
_chem_comp_chir.volume_sign
 33G  chir_01  C4   C14  C18  C5  negativ
 33G  chir_02  C14  C15  C17  C4  positiv

loop_
_chem_comp_plane_atom.comp_id
_chem_comp_plane_atom.plane_id
_chem_comp_plane_atom.atom_id
_chem_comp_plane_atom.dist_esd
 33G  plan-1  F32  0.020
 33G  plan-1  C30  0.020
 33G  plan-1  C29  0.020
 33G  plan-1  C28  0.020
 33G  plan-1  C27  0.020
 33G  plan-1  C31  0.020
 33G  plan-1  C26  0.020
 33G  plan-1  C22  0.020
 33G  plan-1  H1   0.020
 33G  plan-1  H2   0.020
 33G  plan-1  H3   0.020
 33G  plan-1  H4   0.020
 33G  plan-2  C4   0.020
 33G  plan-2  C5   0.020
 33G  plan-2  C10  0.020
 33G  plan-2  C13  0.020
 33G  plan-2  N11  0.020
 33G  plan-2  N12  0.020
 33G  plan-2  C6   0.020
 33G  plan-2  O1   0.020
 33G  plan-2  H23  0.020
 33G  plan-3  C26  0.020
 33G  plan-3  C22  0.020
 33G  plan-3  C21  0.020
 33G  plan-3  C20  0.020
 33G  plan-3  C24  0.020
 33G  plan-3  N25  0.020
 33G  plan-3  C19  0.020
 33G  plan-3  C23  0.020
 33G  plan-3  C18  0.020
 33G  plan-3  C4   0.020
 33G  plan-3  H5   0.020
 33G  plan-3  H6   0.020
 33G  plan-3  H7   0.020

